


Auld Lang Wine (And Scotch)

by story_monger



Category: Supernatural
Genre: F/F
Language: English
Status: Completed
Published: 2015-01-03
Updated: 2015-01-03
Packaged: 2018-03-05 04:09:40
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,076
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/3105110
Author URL: https://archiveofourown.org/users/story_monger/pseuds/story_monger
Summary: <blockquote class="userstuff">
              <p>Ruby is stuck at her boss' New Year party surrounded by coworkers and overpriced wine. Also Anna Milton is infuriatingly gorgeous. Ruby should have gone bar hopping.</p>
            </blockquote>





	Auld Lang Wine (And Scotch)

**Author's Note:**

> Written for a [New Year Fic Exchange](http://jocstiel.tumblr.com/post/106264719606/jocstiel-new-years-fic-exchange-the-year-is)
> 
> Prompt: Annaby at a formal party? Can be AU, canon-verse where they’re dragged into it for whatever reason, anything really. And I’m cool with anything but smut. So if it’s cheesy and fluffy or terrifyingly sad or dramatic, whatever the author feels like writing!

Yeah that settled it: this dress was about three inches too short. Under normal circumstances Ruby wouldn’t have seen this as an issue (it would have been done on purpose, actually) except of all places to accidentally flash your vagina, the company New Year party taking place in the boss’ house was absolutely not one of them.

Ruby tugged at the hem of her dress one more time before giving up and clacking to the bathroom for the…what was it, third time this evening? Someone was going to ask her whether she was feeling sick.

The milling crowd of coworkers parted for Ruby as she slipped through them, smiling woodenly at people she vaguely recognized. No sign of Sam or Dean, which was more than all right by Ruby. With any luck they decided to go out to the bars for their New Year’s celebrations. Ruby would have much preferred bar hopping, herself, but she hadn’t come to the company New Year party for the last two years and at some point, a little social schmoozing with the boss and family had to be borne. Besides, the gift bags were almost always worth the trouble of standing around for several hours trying to make small talk with coworkers while picking at little crackers artistically dabbed with avocado dip.

Ruby emerged from the morass of chatting people and turned into the now-familiar hall leading to the bathroom. The first time Ruby had come to the Milton house (manor? Ruby wouldn’t have been surprised if she was supposed to call the place a manor) she’d honestly expected to find bathroom stalls; it seemed the only way to handle the size of the parties the Miltons frequently hosted. No stalls, it turned out, but the bathroom had two separate rooms, the front one containing several lush couches and a wall-length mirror with a counter. The bathroom itself was no less intimidating; Ruby didn’t think the toilets were anything as mundane as ceramic, but she hadn’t tried to ask anyone about it.

The sound of the crowd became muffled as Ruby let the bathroom door snap shut behind her. No one here; that was a godsend. Ruby marched to the mirror and made a face at her slinky black dress. She really liked this dress, was the thing, and she resented feeling forced to be embarrassed by it. Maybe she should say fuck it and let herself be as inappropriately dressed as she wanted. Give the fogey old folks something to mutter disapprovingly about.

Then again, several of those fogey old people were on the board of directors and probably had some say about her chances for a pay raise. Not to mention Michael Milton, the CEO, was busy trawling the crowd making small talk, along with every one of his siblings, all of whom held positions of varying power within the company. Hadn’t Lilith mentioned something about lay-offs coming up? Ruby didn’t think she was in any danger but still.

“Fuck the Miltons and their fancy better-than-thou parties and their prude board of directors,” Ruby said aloud, just so she could say she’d given a modicum of rebellion. She liked how the words echoed against the genuine marble tile. Then, defeated, Ruby rearranged her dress yet again so that it sat lower on her hips and thighs. It would creep up again within an hour, but maybe if she didn’t move too much she could delay the inevitable—

The toilet flushed. Ruby winced and slowly continued tugging at her dress. That was her luck, wasn’t it? Just watch one of those directors walk out and give her a stink eye. That’d top off the whole night.

Ruby snapped open her clutch and pulled out her blush. Well, let them. She’d already said it and there was nothing for it now but to act as unapologetic as possible. Ruby leaned close to the mirror and reapplied her blush with perhaps more jabbing than light brushes.

The sink turned on and off, and finally the mystery eavesdropper emerged. Ruby caught an impression of dark blue dress and red hair.

Ruby froze. She looked up and nearly said ‘Oh fuck me,’ but held it in at the last minute.

Anna Milton, meanwhile, gave that small, infuriating smile that made her look all grace and beauty and innocence. It was even worse when combined with the dark blue dress that complemented Anna’s breasts and waist in a way that screamed custom tailoring. And it was floor-length.

“Hello Ruby,” Anna said. Ruby twitched.

“Hey,” she said. She weighed her situation then added, “Ms. Milton,” because fool she was not. She’d dug herself into a mother of a pit. And her heart was hammering against her ribs for more varied reasons than Ruby was willing to admit.

Anna, though, didn’t give so much as a hint that she’d just heard an employee cussing out her family in her own house. She just checked her makeup and hair in the mirror (hah, she knew she looked stunning, she just wanted to show off) then smiled at Ruby again.

“I hope you’re having a good time,” she said.

“A blast,” Ruby said through nearly clenched teeth. “Thanks.” She then all but threw her makeup into her clutch, tugged her dress down one more time, then clacked out of the bathroom in heels that, she was suddenly painfully aware, looked precisely like they’d come from the clearance rack at T.J. Maxx.

***

Forty minutes to midnight, and Ruby was spending her last hour of 2014 standing at the edge of a loose circle of accountants with glass of severely overpriced wine in one hand and the other hand surreptitiously tugging at the hem of her dress. Crowley and Zachariah were still dominating the conversation with talk of returns for the last quarter, so Ruby tuned them out. She instead admired the tall windows, glittering chandelier, and downright magical ropes of real pine and old-fashioned tinsel strung along the grand bannister. The Christmas tree in the main hall could have come straight from the Nutcracker and the air had the faint smell of cinnamon and cloves.

Ruby grunted and downed her wine. She could finally feel the three glasses she’d had earlier starting to affect her. Thirty-five minutes to go.

“If only the production team hadn’t screwed up quite so grandly,” Crowley said. “We could have seen a 12 percent increase.”

Ruby shifted her weight from one foot to the other then stiffened. Anna Milton and her well-tailored dress had reappeared. She was scanning the crowd, smiling at people absently, then seemed to hone in on Ruby’s corner of the room and started striding forward with greater purpose. Ruby gritted her teeth and was about to conjure an excuse to slip away when, miracle of miracles, her phone buzzed.

“Gotta take this, fellas,” she burst out, making Crowley and Zachariah both blink and turn to her. “Damn that production team, am I right? Be right back.”

Ruby ducked away before they could answer.

A quick glance at the screen showed Meg’s name, and Ruby nearly laughed. Leave it to her sister to save Ruby’s ass.

“Y’ello,” Ruby said as she put the phone to her ear. She almost immediately had to wince and yank it away when a low thumping rattled through the speaker. Ruby edged behind the refreshment table and grabbed another glass of wine while she was at it.

“Meg?” She tried to yell without actually yelling.

“HEY!” Meg’s voice clattered over the bass. “You still a’ tha’ lame comp’ny party?”

“Yeah and you’re trashed,” Ruby said.

“Dude so trashed,” Meg exulted. “You comin’ over or what?”

“Probably not.”

“Awwww,” Meg whined. “You said you would though!”

“I said I’d think about it.”

“Nooo, you said you’d come. Here…here, Al? Didn’t Ruby say she’d come?” Ruby took a sip from the wine as a male voice said something indistinct in the background. “Hah,” Meg said a second later. “He says yeah.”

“Listen, I’ve been here this long,” Ruby said. “Might as well see it through to midnight. I’ll come right after that though, okay?”

“Ugh,” Meg groaned. “Fine. Boring.”

“Yeah sure. By the way, thanks a lot for messing up the red dress. I’m totally dressed wrong for this, I told you this one wouldn’t work.”

“’t’s black tie, right?” Meg asked around the sound of something wet and smacking. Ruby didn’t ask.

“Right.”

“So you havva black dress. You’re fine.”

“You’re no help,” Ruby groused. “You don’t understand, it’s…” She scanned the main hall. The men in tuxedos and the women in long gowns made the scene look like something from a movie. A movie in which Ruby absolutely did not belong. She was worse than an extra, she was an extra from the movie being shot in the next studio over and had wandered over here on accident and someone with a clipboard and a headset was going to come over here soon and shoo her away.

“It’s what?” Meg asked, followed by a more distant, “Al, get off me a second.”

“Nothing,” Ruby sighed. “I’m just…I cussed out the family in the bathroom and I’m about 99 percent sure that Anna Milton heard me.”

“Anna? Your boss?” Meg paused thoughtfully. The thumping bass changed rhythm into something faster. “She’s stuck up,” Meg stated after a moment.

“You should have seen her.” Ruby leaned against the wall and nearly drained her glass. “Parading around in this gorgeous blue dress that probably cost my annual salary. Hair all coiffed. Makeup, like, this perfect shade. Just like she always is at the office but worse.”

“P'rfect makeup, huh? Maddening,” Meg said, and Ruby could hear the wide grin. Ruby scowled.

“She was right in my face,” she defended herself.

“Sure. I don’ think the dress was y’r salary though,” Meg said. “You make a lot, ‘specially after that promotion, an’ they can’t be tha’ rich.”

“Dunno, the Miltons are sort of a mogul,” Ruby said, watching couples wander past. “I heard that—oh shit.”

“What?”

“The moose and his brother are here.”

“Darn,” Meg said sympathetically.

“I gotta go,” Ruby said, eyes fixed on Sam Winchester as he maneuvered around the crowd, at least a head taller than most of the people around him. Beside him, Dean looked about as suave in his tuxedo as Ruby would expect.

“’Kay don’t forget—“ Ruby didn’t hear what Meg wanted her not to forget as she hung up, set the empty wine glass back on the table, and started to edge along the wall. Neither Sam nor Dean had looked in her direction, but Ruby wasn’t about to tempt fate. Instead she made it to a smaller side staircase (not the grand staircase, mind) and darted up. She waited for someone to shout at her to come down, but the chatter below remained undisturbed. Ruby reached the landing and chanced a glance over the bannister.

From this vantage point, the party had even more of a fairytale look. Everything looked clean and sparkling and sumptuous. The ladies graceful, the men gallant, the waiters and waitresses smart with their silver trays. The tower of champaign and the string quartet playing something from Mozart were just the last straws.

Ruby hovered at the bannister a few moments later then retreated before someone spotted her. Technically speaking she knew she shouldn’t be on the second floor, but hopefully she could claim she’d gotten lost if the butler or someone found her.

(Did the Miltons have a butler? Ruby decided yes.)

Ruby took another look around her then chose a direction and started walking down the hallway. She figured she ought to squeeze in as much snooping as she could before being unceremoniously tossed out.

Ruby had been fully expecting to find gold-plated doors and lines of family portraits, maybe a Renoir somewhere in there. And true, the carpet was thicker and nicer than the carpet in Ruby’s small, old house, and the walls were clean and bright and they had a few paintings hanging up. But when Ruby paused to scrutinize them, the paintings seemed to feature mostly landscapes and boats on bright blue seas.

Ruby passed little tables with neatly organized picture frames featuring chubby, bald babies and staring toddlers, stiff school pictures and grinning graduation pictures. The Milton family, Ruby found. She could pick out the late Charles Milton, all smiles and wild hair. Naomi Milton with just as much poise if not fewer wrinkles. The four oldest boys, Michael, Lucifer, Raphael, and Gabriel, all looked appropriately handsome in various suits and graduation gowns. (They were the heartbreak of many a woman in the company; Ruby knew of at least three people who had the contingency plan of trying to marry one of the Milton boys and cashing into the fortune).

Anna and the baby of the family, Castiel, were notably younger than their siblings. They seemed to stay together in family portraits, Ruby decided; Castiel serious and Anna shy. Ruby paused at one picture of the two of them. Anna looked to be middle school age, Castiel somewhere around fifth grade. They stood among pine trees, their arms around each other and their smiles wide. Anna had hot pink braces and pimples and looked like she’d yet to discover makeup or properly fitting clothes; Castiel looked flushed and too skinny. Ruby picked it up and studied the small grainy faces. They looked like any other gawky pair of thick-as-thieves siblings, and it took a moment for Ruby to realize she was grinning at the picture.

Ruby didn’t register the door next to her opening until too late, and by the time she looked up, Anna had already released a small, surprised, “Oh.”

Ruby had heard the term “blood drained from her face.” This was the first time she’d experienced it quite so thoroughly. She imagined public disgraces and immediate firing. Sam and Dean probably looking all smug in the background.

When Anna didn’t break the silence quickly enough, Ruby’s nervous energy took over.

“Hey, I’m sorry,” she said, smiling plastically. “I got lost.”

Anna blinked and then rubbed at one eye. Ruby waited to see whether the makeup had been smeared. It hadn’t. Ruby had no choice but to suspect witchcraft.

“It’s okay,” Anna said in a rough, graveled voice that spoke very little of well dressed upper class and more of chain smoking cook in a greasy spoon diner. It nearly made Ruby jerk. “I needed to get out of there too.”

“I didn’t…” Ruby rolled in her lips and let whatever half-assed excuse she’d been formulating die away. Anna didn’t look like she was in the mood for it. She didn’t look like she was in the mood for anything except maybe disappearing into her bed.

“Did something happen?” Ruby found herself asking.

Anna’s head lifted slightly and the corner of her mouth twitched.

“My brother’s mad at me,” she said.

“Oh.” Ruby frowned. “Which one?”

“That one.” Anna nodded at the picture of Anna and Castiel still in Ruby’s hands. Ruby hurriedly set it back in its place, cheeks flushing.

“Well, that’s pretty normal,” Ruby said in too cheerful a voice. “I hate my sister every so often.”

“Yeah?” Anna leaned against the wall and tilted her head as she continued to scrutinize Ruby. Anna’s red hair slipped across her shoulder, over an ivory white collarbone and the beginning swells of her breasts. Ruby blinked hard and reminded herself, as always, that this was her stick-in-the-ass millionaire boss and thus way out of Ruby’s league. Way, way out.

“Sure,” Ruby said. “It’ll blow over in, like, a week I bet.”

“Dunno,” Anna frowned and crossed her arms. She seemed to think for a moment before she straightened and looked at Ruby with a set jaw. “See, the problem is that I hooked up with Dean Winchester three nights ago without realizing that my baby brother’s been carrying a torch for this guy for years and now Cas is heartbroken and angry and pretending not to be.”

Ruby stared.

“You and Dean Winchester?” Ruby finally managed. (No, she wasn’t jealous, she told herself. Not at all. Shut up.) “I didn’t realize you knew each other.”

“Not well. He’s in advertising and I mainly work with the legal offices. But, y’know. We met up at a bar on accident and things happened.” Anna made a face. “I had an inkling that Cas had a thing for Dean a couple years ago, but I thought that had blown over. This was just a hook up, but that wouldn’t matter to Cas, would it? He’s head over heels for this guy.”

“I had no idea Cas swung that way,” Ruby said.

“Yeah, neither does the rest of the family except for me,” Anna said resignedly. She paused when a swell of laughter rose from the first floor. “It just makes this whole thing worse,” she continued. “Because if Cas ever dated Dean, ever came out, Michael’s liable to disown him. Then I come along and have Dean for a night without a hitch and it’s like salt in the wound, you know?”

“Geeze,” Ruby tugged at the hem of her dress absentmindedly. “That does suck.” She looked sidelong at Anna. “So you’re hiding from Cas?”

“From Cas and Dean both,” Anna sighed. “I don’t want to get caught up in all that, any more than I already have.”

“Well, join the club I guess,” Ruby shrugged. “I came up here to hide from Winchesters too.”

“What? Really?” Anna frowned.

“Yeah, I pissed them off when I…” Ruby paused. She could taste the wine on her tongue.

“What?” Anna leaned forward.

“It wasn’t illegal,” Ruby blurted. “But it was definitely a dick move on my part.”

“Well now you have to tell me.”

Ruby sighed and tugged at her dress again.

“I might have fed Sam Winchester some half truths about available positions in the international offices. And he might have believed them. And it might have left him screwed over. And that might have translated into Dean looking for blood because the Winchesters are a weird family.”

“Why?” Anna asked, face crumbling.

“I dunno, I hear they grew up travelling all over the country—“

“No, why do that to Sam?”

“He wasn’t badly screwed over,” Ruby protested. “He’s smart; he’ll be fine. It’s just the student loans are getting harder to pay and I really needed the promotion and…shit, why am I telling you this?”

Anna tilted her head then pushed herself from the wall with a small sigh.

“It’s okay,” she said dully. “That sounds like small beans compared to what my brothers have done.” Anna shrugged again. “I don’t care enough to chew you out right now.”

“Wow, really?” Ruby squinted at Anna. “You really must be feeling crappy.”

“What’s that supposed to mean?”

“Yeah, usually you’re Miss Law and Order, nag us all to death, cracking the whip of justice.”

“I’m not that bad,” Anna protested, a small smile curling into the corner of her mouth.

“You’re totally that bad,” Ruby said.

They paused again when the chatter died down. A single masculine voice echoed up to them.

“That’s Michael,” Anna said. “Must be close to midnight.”

“We have about twenty minutes,” Ruby agreed.

The two women watched one another for another long moment.

“I have a bottle of scotch in my room. Want to drink it while we see the rest of the house?” Anna finally asked. “We can keep avoiding Winchesters that way.”

Ruby felt her mouth twitch.

“Yeah okay,” she said.

Anna turned, her blue ball gown rustling. Ruby followed in her too-small dress and T.J. Maxx heels.

***

“You have a green house,” Ruby said, gazing at the jungle of flowers around them. “Of fucking course you have a green house.”

“Nooo,” Anna protested. She reached for the bottle of scotch—nearly half gone—and Ruby held it just out of reach for several seconds before giving in. Anna looked too cute to be deprived of alcohol.

“Yeah, it’s so stereotypical,” Ruby said. She poked at a daylily. “What, do you have a bowling alley in the basement?”

“Nah.” Anna hiccupped. “Dad hated bowling.” She passed the bottle back over.

Ruby could smell Anna’s perfume, distinct among the many blossoms surrounding them. Ruby took a massive swig of the scotch.

When she lowered the bottle, she looked over and found Anna staring into space. Anna was one of those people who had the god-given talent of looking gorgeous even while transparently morose. The contrast was giving Ruby a headache.

As if feeling Ruby’s stare, Anna glanced over.

“What?” she asked.

“Nothing,” Ruby lied. She could feel the scotch mixing with the wine, making a dangerous warmth spread through her lower belly. “I just now remembered I’m supposed to hate you and that I’m doing really badly at that right now.”

“Oh yeah,” Anna smiled lopsidedly. Ruby discovered that Anna could also look gorgeous and adorable at the same time. Unfair. “You gave me a really good stink eye in the bathroom earlier. Ten out of ten.”

“Sorry,” Ruby said. She paused. “Nah, not sorry. I meant it. These parties are the worst and your family comes off as irredeemable snobs.”

“God, don’t we?” Anna leaned forward. “I know I’m as guilty as my mom and brothers, that’s almost the worst part.”

“Hey, admission is the first step toward recovery,” Ruby reminded Anna. “You might be okay in the end.” Ruby stole another sip from the scotch.

“But that was also a pretty rude thing for you to say,” Anna added. “So fuck you.”

“Fuck you too,” Ruby grinned. She passed the bottle. “Truth talk here; how bad was this dress for your shin-dig?”

Anna leaned back and looked Ruby up and down. Ruby had to suppress the small shiver that crawled up her spine.

“Massively so,” Anna finally said. “I’m pretty sure the invitation said formal black tie.”

“I had a better dress,” Ruby groaned. “But then my sister borrowed it two days ago and ruined it. With puke. I didn’t have time to find anything better.”

“Damn,” Anna commented. She tilted her head, and her hair did that falling-gracefully-over-her-clavicle thing again. “It’s probably for the better though,” she said. “You have a great ass and cute legs. Shame to cover them.”

Ruby coughed. She kept coughing. She leaned over and hacked a few times.

“You okay?” Anna’s dress rustled like several birds taking flight as she bent over to see Ruby’s face.

“Awesome,” Ruby rasped. She tilted her head and straightened slowly. “Anna Milton, I think you’re flirting with me.”

“Sorry,” Anna said, not sounding very sorry at all. “I forgot, you’re supposed to hate me.”

“I don’t hate you very much,” Ruby decided. Exactly the opposite, probably. But Ruby had not drunk quite enough scotch for that.

But apparently she had drunk enough to say, “You have a deep dark secret to keep from Michael too, then?” Because she had to know. She couldn’t leave this situation without at least _knowing_.

“I guess so. Not in such a bind as Cas,” Anna shrugged. “I’m bi, so at least I can publically romance half of the available pool. Poor Cas is thoroughly into dick.”

“Oh,” Ruby said in a high voice, managing some pity for Castiel but largely interested in the other part. Because bi was good. She could work with bi.

Ruby took another swig to calm her nerves and passed the bottle back over. Her eyes fell on her phone sticking halfway out of her clutch. It read 12:16.

“It’s 2015,” Ruby said. “Happy New Year.”

“Auld Lang Syne,” Anna said. She rotated the scotch bottle in her lap, making the fabric rustle. Ruby watched this and, in a great thunderclap of realization, decided that this was the kind of situation that only novelists would be able dream up. She had some kind of obligation to sad lesbians everywhere crushing on their impossibly gorgeous and wealthy bosses to make the most of this.

“You’re staring again,” Anna said. She was smiling.

“Dunno, you’re kinda cute,” Ruby said, and hardly stumbled over her words at all. Anna’s smile widened, and after a moment, she leaned forward.

“Okay,” Ruby murmured mostly to herself, and leaned in to meet her.

Anna Milton tasted like scotch underlain with white wine and something like avocado dip. Ruby grinned into Anna’s mouth.


End file.
